Determination of partition coefficients for several highly-fluorinated, alkoxysubstituted bisarylferrocene derivatives

CHED 807

Matthew G. Poferl1, W. Gary Hollis1, and Paul A. Deck2. (1) Department of Chemistry, Roanoke College, 221 College Lane, Salem, VA 24153, (2) Department of Chemistry, Virginia Tech, 107 Davidson Hall, Blacksburg, VA 24061-0212
The preparation and characterization of seven fluorinated derivatives of ferrocene was accomplished in order to determine their partition coefficients between two solvent environments, one fluorous and one organic. Between toluene and perfluoromethylcyclohexane, the partition coefficients, Concentration in Perfluoromethylcyclohexane/Concentration in Toluene, were found to be 0.0539 for 1,1’-bis(2,2,3,3,4,4,4-heptafluoro-1-butoxytetrafluorophenyl)ferrocene (3), 0.3676 for 1,1’-bis(2,2,3,3,4,4,5,5,6,6,7,7,7-tridecafluoro-1-heptoxytetrafluorophenyl)ferrocene (4), 0.8191 for 1,1’-bis(2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluoro-1-octoxytetrafluorophenyl)ferrocene (5), 1.1384 for 1,1’-bis(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,9-heptadecafluoro-1-nonoxytetrafluorophenyl)ferrocene (6), 2.0962 for 1,1’-bis(2,2,3,3,4,4,5,5,6,6,7,7,8,8,9,9,10,10,10-nonadecafluoro-1-decoxytetrafluorophenyl) ferrocene (7), and 1.6752 for 1,1’-bis(2,2,3,3,4,4,5,5,6,6, 7,7,8,8,9,9,10,10,11,11,11-heneicosafluoro-1-undecoxytetrafluorophenyl)ferrocene (8). Between hexanes and perfluoromethylcyclohexane, the partition coefficients, Concentration in Perfluoromethylcyclohexane/ Concentration in Hexanes were found to be 0.7296 for compound 3, 1.2506 for compound 4, 1.3277 for compound 5, 1.4632 for compound 6, 1.9019 for compound 7, and 1.9415 for compound 8.